MiMeDB: Showing metabocard for Tryptoquivaline H (MMDBc0014365)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 05:24:52 UTC

Update Date

2022-08-31 06:37:35 UTC

Metabolite ID

MMDBc0014365

Metabolite Identification

Common Name

Tryptoquivaline H

Description

Fumitremorgin E belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. Fumitremorgin E is a moderately basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152107242D          

 34 39  0  0  1  0            999 V2000
    0.9505    2.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1618   -3.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4962    1.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3432   -3.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568    2.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6598   -3.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9322    1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -2.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534    2.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750    0.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979   -0.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7299    2.2148    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3391   -2.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1288    1.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5205   -2.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894    2.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145   -0.3501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4068    2.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371   -1.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8393   -0.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7942    1.4090    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4519    0.9110    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1999   -1.5632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5165   -1.0079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645    2.1885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9693    1.4253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4230    3.5113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557   -1.8704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3110   -1.0433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4713    0.7675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1097    0.4130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6169    3.0320    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3744   -1.0925    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5837    1.6484    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 12  1  1  1  0  0  0
 13  6  2  0  0  0  0
 14  7  2  0  0  0  0
 15  8  2  0  0  0  0
 15 13  1  0  0  0  0
 16  9  2  0  0  0  0
 16 14  1  0  0  0  0
 17 10  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 17  1  0  0  0  0
 22 10  1  0  0  0  0
 22 14  1  0  0  0  0
 22 21  1  0  0  0  0
 23 11  2  0  0  0  0
 23 15  1  0  0  0  0
 24 11  1  0  0  0  0
 17 24  1  6  0  0  0
 24 19  1  0  0  0  0
 25 16  1  0  0  0  0
 25 18  1  0  0  0  0
 25 21  1  0  0  0  0
 26 12  1  0  0  0  0
 26 21  1  0  0  0  0
 27 18  2  0  0  0  0
 28 19  2  0  0  0  0
 29 20  2  0  0  0  0
 30 26  1  0  0  0  0
 31 20  1  0  0  0  0
 22 31  1  6  0  0  0
 12 32  1  6  0  0  0
 17 33  1  1  0  0  0
 21 34  1  1  0  0  0
M  END


  Mrv1652305152107242D          

 34 39  0  0  1  0            999 V2000
    0.9505    2.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1618   -3.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4962    1.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3432   -3.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568    2.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6598   -3.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9322    1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -2.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534    2.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750    0.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979   -0.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7299    2.2148    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3391   -2.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1288    1.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5205   -2.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894    2.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145   -0.3501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4068    2.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371   -1.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8393   -0.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7942    1.4090    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4519    0.9110    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1999   -1.5632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5165   -1.0079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645    2.1885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9693    1.4253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4230    3.5113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557   -1.8704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3110   -1.0433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4713    0.7675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1097    0.4130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6169    3.0320    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3744   -1.0925    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5837    1.6484    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 12  1  1  1  0  0  0
 13  6  2  0  0  0  0
 14  7  2  0  0  0  0
 15  8  2  0  0  0  0
 15 13  1  0  0  0  0
 16  9  2  0  0  0  0
 16 14  1  0  0  0  0
 17 10  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 17  1  0  0  0  0
 22 10  1  0  0  0  0
 22 14  1  0  0  0  0
 22 21  1  0  0  0  0
 23 11  2  0  0  0  0
 23 15  1  0  0  0  0
 24 11  1  0  0  0  0
 17 24  1  6  0  0  0
 24 19  1  0  0  0  0
 25 16  1  0  0  0  0
 25 18  1  0  0  0  0
 25 21  1  0  0  0  0
 26 12  1  0  0  0  0
 26 21  1  0  0  0  0
 27 18  2  0  0  0  0
 28 19  2  0  0  0  0
 29 20  2  0  0  0  0
 30 26  1  0  0  0  0
 31 20  1  0  0  0  0
 22 31  1  6  0  0  0
 12 32  1  6  0  0  0
 17 33  1  1  0  0  0
 21 34  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0014365

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(C)N(O)[C@]2([H])N(C1=O)C1=CC=CC=C1[C@@]21C[C@@]([H])(N2C=NC3=CC=CC=C3C2=O)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H18N4O5/c1-12-18(27)25-16-9-5-3-7-14(16)22(21(25)26(12)30)10-17(20(29)31-22)24-11-23-15-8-4-2-6-13(15)19(24)28/h2-9,11-12,17,21,30H,10H2,1H3/t12-,17+,21-,22-/m0/s1

> <INCHI_KEY>
LSEZQEFBFFRCNW-TYTLQBBQSA-N

> <FORMULA>
C22H18N4O5

> <MOLECULAR_WEIGHT>
418.409

> <EXACT_MASS>
418.127719696

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
41.554251059065365

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4'R,9S,9aS)-1-hydroxy-2-methyl-4'-(4-oxo-3,4-dihydroquinazolin-3-yl)-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-3,5'-dione

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
1.1606668626666672

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.60568359782272

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.922229993990126

> <JCHEM_PKA_STRONGEST_BASIC>
2.687589276386899

> <JCHEM_POLAR_SURFACE_AREA>
102.75

> <JCHEM_REFRACTIVITY>
108.63519999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4'R,9S,9aS)-1-hydroxy-2-methyl-4'-(4-oxoquinazolin-3-yl)-2,9a-dihydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-3,5'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       1.774   4.639   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.035  -7.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.260   3.355   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.507  -6.984   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.813   4.829   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.965  -5.947   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.207   2.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.909  -5.565   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.313   5.179   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.180   0.820   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.169  -1.690   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.229   4.134   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.366  -4.528   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.707   2.581   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.838  -4.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.260   4.055   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.627  -0.654   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.493   5.015   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.296  -3.300   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.167  -0.684   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.216   2.630   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.444   1.701   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       2.240  -2.918   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       4.697  -1.881   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       5.720   4.085   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0       3.676   2.661   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0       4.523   6.554   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.824  -3.491   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       8.047  -1.947   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.746   1.433   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       7.671   0.771   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0       3.018   5.660   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       6.299  -2.039   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       6.689   3.077   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2    4    6                                                       
CONECT    3    5    7                                                       
CONECT    4    2    8                                                       
CONECT    5    3    9                                                       
CONECT    6    2   13                                                       
CONECT    7    3   14                                                       
CONECT    8    4   15                                                       
CONECT    9    5   16                                                       
CONECT   10   17   22                                                       
CONECT   11   23   24                                                       
CONECT   12    1   18   26   32                                             
CONECT   13    6   15   19                                                  
CONECT   14    7   16   22                                                  
CONECT   15    8   13   23                                                  
CONECT   16    9   14   25                                                  
CONECT   17   10   20   24   33                                             
CONECT   18   12   25   27                                                  
CONECT   19   13   24   28                                                  
CONECT   20   17   29   31                                                  
CONECT   21   22   25   26   34                                             
CONECT   22   10   14   21   31                                             
CONECT   23   11   15                                                       
CONECT   24   11   17   19                                                  
CONECT   25   16   18   21                                                  
CONECT   26   12   21   30                                                  
CONECT   27   18                                                            
CONECT   28   19                                                            
CONECT   29   20                                                            
CONECT   30   26                                                            
CONECT   31   20   22                                                       
CONECT   32   12                                                            
CONECT   33   17                                                            
CONECT   34   21                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

Synonyms

Not Available

Molecular Formula

C₂₂H₁₈N₄O₅

Average Mass

418.409

Monoisotopic Mass

418.127719696

IUPAC Name

(2S,4'R,9S,9aS)-1-hydroxy-2-methyl-4'-(4-oxo-3,4-dihydroquinazolin-3-yl)-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-3,5'-dione

Traditional Name

(2S,4'R,9S,9aS)-1-hydroxy-2-methyl-4'-(4-oxoquinazolin-3-yl)-2,9a-dihydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-3,5'-dione

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C)N(O)[C@]2([H])N(C1=O)C1=CC=CC=C1[C@@]21C[C@@]([H])(N2C=NC3=CC=CC=C3C2=O)C(=O)O1

InChI Identifier

InChI=1S/C22H18N4O5/c1-12-18(27)25-16-9-5-3-7-14(16)22(21(25)26(12)30)10-17(20(29)31-22)24-11-23-15-8-4-2-6-13(15)19(24)28/h2-9,11-12,17,21,30H,10H2,1H3/t12-,17+,21-,22-/m0/s1

InChI Key

LSEZQEFBFFRCNW-TYTLQBBQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Diazanaphthalene
Quinazoline
Indole or derivatives
Pyrimidone
Gamma butyrolactone
Imidazolidinone
Pyrimidine
Benzenoid
Tetrahydrofuran
Tertiary carboxylic acid amide
Heteroaromatic compound
Imidazolidine
Carboxamide group
Carboxylic acid ester
Lactone
Lactam
N-organohydroxylamine
Organoheterocyclic compound
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	1.13	ALOGPS
logP	1.16	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.92	ChemAxon
pKa (Strongest Basic)	2.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	102.75 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	108.64 m³·mol⁻¹	ChemAxon
Polarizability	41.55 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	3	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

158572

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

182322

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Tryptoquivaline H (MMDBc0014365)

MOL for #<Metabolite:0x00007feca8a3e840>

3D MOL for #<Metabolite:0x00007feca8a3e840>

3D SDF for #<Metabolite:0x00007feca8a3e840>

3D-SDF for #<Metabolite:0x00007feca8a3e840>

PDB for #<Metabolite:0x00007feca8a3e840>

3D PDB for #<Metabolite:0x00007feca8a3e840>

SMILES for #<Metabolite:0x00007feca8a3e840>

INCHI for #<Metabolite:0x00007feca8a3e840>

Structure for #<Metabolite:0x00007feca8a3e840>

3D Structure for #<Metabolite:0x00007feca8a3e840>